The Dilemma
by GoingVintage
Summary: After yet another disagreement with Felicity, Oliver lets himself into her apartment to make things right and finds himself caught in the best sort of hell. PWP. Voyeur!Oliver.


Oliver Queen had always been selfish land he knew it. Selfish in life, selfish in love, and damn selfish when it came to pleasure. Sex, to him, had been much more about the actual conquest than the pleasure. Daddy's little princess. The frigid daughter of the police commissioner. The occasional supermodel who stumbled her way into Starling City and ended up at the same club where he and Tommy had a table reserved. Sure, he loved getting off as much as the next guy, and he sure as hell enjoyed the sight of a pair of cherry red lips wrapped around his cock, but even he would admit that making sure the woman got off, too, hadn't been on the top of his list.

Then the Queen's Gambit went down and his life turned into five years of loss and misery and unmitigated hell. Even now, six years after the disastrous night that charted a new path for his life, he had only chipped off and shared a small portion of his history with his closest friends. He wasn't the same guy. He'd gotten rid of that ridiculous hair. Learned to face and accept consequences to his actions. Recognized that he'd been…well…kind of a prick. He believed he'd gotten more generous with the ladies, too. (He still remembered a conversation he'd had with Slade back in the early days, before the mirakuru had fucked up his world. They'd been sitting around the fire in one of those rare moments of relaxation, swapping stories about the chicks they'd nailed back home. "Two and then you," Slade had told him, his eyes twinkling over the firelight. When Oliver had prodded him for more information, Slade had explained, "Make sure she comes twice before you come at all. You'll be repaid in spades. Trust me.") And now, instead of surrounding himself with people who looked into his eyes and saw the reflection of his bank account balance in them, he only associated with those who had strength and conviction. Strong character. A moral compass. And, as he was learning more and more every day, one who knew how to hold a helluva a grudge.

…

"Felicity, we need to talk about this."

The hand that flew into his face made him stop short, his dress shoes squeaking on the floor of the lair. "We have nothing to talk about, Oliver. Once again, you're making an idiotic mistake. You seem to be making them more frequently, which makes me question if you're not losing your focus, but that's neither here nor there right now. Either way, I've said all I'm going to say and now the choice is up to you. Just, for once, think about the ramifications of your actions, okay?" Felicity bent over to grab her huge purse, and Oliver couldn't help but notice the way the periwinkle slip of a dress she was wearing clung to her thighs.

"Don't leave." Oliver reached for her arm. "You always leave mad and then we have, like, two days where things are awkward and then I apologize and you forgive me and we start the cycle all over." He shoved his hand through his hair. "I'm too tired to go through that, Felicity. Just hear me out. I'm making a smart decision this time."

The snort that came from Felicity would've made him grin if hadn't been so irritated.

"I'm going home. Don't call me. Don't text me. Don't IM me. I'm going to have some much-needed 'me' time, which I never get because I'm always here, getting you out of jams and erasing your inadvertent sex tapes. When I come into the office tomorrow, we'll talk. Until then, have a lovely night."

Felicity turned on her impossibly high heels and stomped toward the door, her firm calves rippling with each step. Oliver couldn't help but appreciate watching her retreat, even as her latest admonishment stung.

"She has a point." Diggle's voice cut through Oliver's thoughts.

"You always take her side."

"That's because she's usually right." Diggle clapped his hands together. "Anyway, our work here is done." He clasped Oliver on the shoulder. "I'll see you in the morning, man."

Oliver nodded, staring at the computer screens in front of him while Diggle left the lair. When there was nothing to keep him company except the sound of his loneliness, Oliver spun on his heel and grabbed his bow. Leave Felicity alone? Not likely. Not this time.

…

Felicity lived in a shitty building, Oliver decided, if you could judge a place solely based on the quality of the fire escapes. This particular fire escape hung precariously to the brick, the bolts rusted in places and missing from others. By the time he'd slipped down from the roof and stood on the landing outside her twelfth floor window, he was amazed that he hadn't plummeted to the street below.

Thunder was now rumbling over the city, a storm rolling in from the west. Lightning ricocheted from cloud to cloud above him, the air swirling around him full of electrical charge. It heightened his senses, made his blood rush faster. The rain started slowly, pattering on the metal by his feet and sluicing down his hood as he stared at the darkened window in front of him. It didn't look like Felicity was even home, but Oliver knew she hadn't gone anywhere. She was too much of a homebody. He stood still and silent, sucking in a deep breath of energy-charged wind, and pressed against the glass. Through the crack in the curtains, he could see that her living room was deserted. Straining his eyes to the left, he could see that her bedroom door was partially opened and there, a sliver of light was visible.

The window opened with very little pressure and then Oliver was inside. His feet landed soundlessly on the plush carpet, where he laid down his bow and quiver. Pushing his hood off, he lifted the mask off his face and slid it into his pocket as he walked toward the open door. As he drew closer, he realized that the light came from a flickering television, although he couldn't hear any sound. It wasn't totally quiet, though, and as he stepped up to the door, his ears were greeted by a noise he couldn't place.

Buzzing.

Soft, steady buzzing.

Pressing his eye up to gap created by the almost-closed door, Oliver's only view was of an open closet. Clothes were strewn about, spiky heels spilling from a large plastic tub. He smiled to himself, never having realized that Felicity was a slob, when a sound made his breathing choke off.

A moan.

Fingers on the door, he nudged it open another inch.

Still nothing.

One more inch.

Then another.

The edge of Felicity's bed came into view, along with a set of pink-tipped toes, and another moan mingled with the thunder clapping outside.

Curiosity fuelling him, he pushed the door open two more inches. The sight before him made his mouth fall open, his mind skidding to a halt as the blood rushed from his brain.

Felicity was lying on her bed, legs splayed open like an invitation. Bare from the waist down, she had a…

Oliver cocked his head. What the hell?

His mouth went dry, his tongue turning to dust as Felicity slipped her hand to the hem of the pink t-shirt she wore and pushed it up, baring her breast to the room. The soft swell of skin, tipped with a coppery nipple that was beading to a point, made him bite his lip to keep from groaning. He watched as she trailed her fingers over her skin and then she was twisting that little point between them.

_Holy shit._

Felicity shifted down the mattress as she pulled her legs up, her feet now flat on the bed. Knees open wide, Oliver could only stare, slack-jawed, at what he was seeing. Royal blue straps hugged her trim thighs and seated between them was a… butterfly? Blue and obviously rubber, it vibrated against her cleft, blocking from his view what he knew would be a beautiful pussy.

_Holy fucking shit. _Felicity was getting herself off with a vibrator.

The soft sighs coming from her mouth made Oliver swallow against the hard pulse of desire that seemed to beat in every part of his body. He'd heard her laugh and cry and babble and swear, but he'd never, _ever _heard her make that sound. And now, in a split second, he wondered how the hell he'd lived without it.

_Fuck. Fuck. Fuck._

The sound of vibrating increased as Felicity fumbled with the remote control in her hand. As the butterfly buzzed more intensely against her center, Felicity groaned and arched her back. Her hand slid down her stomach and settled right on the tiny little thatch of hair covering her mons. Her fingers seemed to dance along her skin, tapping and teasing, but never applying enough pressure to really do anything for her. She responded, though, her hips rocking as she increased the speed once again.

Oliver's cock throbbed against his leather pants. The whole commando thing seemed less than brilliant now that he sported a raging erection. These pants weren't made for hard-ons.

"Oh, God. _Yes._" Felicity rocked her hips upward, her finger sliding beneath the vibrator. Oliver knew the minute she pressed against her clit because a sob, this throaty little cry so beautiful that it made his heart clench while his dick throbbed, tumbled from her lips. "Ohhhh," she moaned again.

A bright flicker from the television cast a few seconds of blue light on Felicity's body. Natural beauty illuminated by that unnatural flash, Oliver could see that her thighs were wet, slick from her own desire. He bit his lip and leaned against the door jab, his hand settling against his hard cock, squeezing the leather around it in a lame attempt to ease the pressure. Even while he watched her, he could barely believe what he was seeing. Felicity was so… _not _like this. No, his Felicity babbled and flooded his world with ridiculous rambling, but she was whip smart and dependable and… _not like this_.

Realization and desire and the drumming of need like he'd never felt before made him want to push the door open and sink his face between her legs. He was a much more generous lover than he'd used to be, and his lips tingled with the desire to surround her hard little clit, his tongue sinking into her. He somehow knew she'd taste spicy and tangy. He could tell that she'd bury her fingers his hair and ride his face until she came. Felicity wouldn't be shy when it came to taking what she needed. Hell, no, and the idea thrilled him.

Before he had a chance to act, Felicity's body jerked and the sound of her orgasm filled his ears. Her eyes clamped tightly closed while her hips shook, one hand pressing the vibrator firmly against her body.

Oliver was afraid to take a breath for fear that she'd know he was there. His hand slipped inside his pants and he stroked his cock once, squeezing it at the base and then gliding his hand up to the fat crown. He was going to burst. He contemplated slipping back out into the night and letting the rain wash away the hunger and craving and the newfound knowledge that he knew had just altered the reality of his very unordered world.

The buzzing stopped, making Oliver jerk his hand from his cock and take a step back into the darkened front room. Felicity moved on the bed, lifting her hips up and then her legs as she slid the butterfly's straps down and then off. He expected her to grab a pair of panties, slide them on, and end this torture that he found himself in. Hell, he _wanted _her to, just so he could give himself twenty minutes of standing outside in the soaking rain while he got his shit together before he knocked on her window and pretend that their last interaction had been fighting, not witnessing her lost in her own body.

The sound of her sighing made him peer back into the room and, once again, he managed to be surprised. She was dragging her t-shirt up and over her head. It floated to the floor, nearly landing at his feet, and then she was completely naked. She sat up on the bed, turning to reach into her bedside drawer. He watched her in profile, the way her skin stretched across her ribs. The way her breasts moved as she yanked open the drawer that was obviously stuck. The way her shoulder flexed as she reached inside. She made a satisfied sound as she pulled her hand out, her fingers curling around a thick, phallic dildo.

_Son of a bitch, _Oliver mouthed. He was in the _worst _sort of hell. In that moment, no stab would or bullet hole or burnt flesh, torn and gaping and oozing blood, was worse than watching this beautiful, lithe woman pull her knees up against her chest, open her legs wide, and slide the tip of that toy between her wet folds. And Jesus, she was dripping. Pink lips, fat from desire, called to him. He could hear the soft sucking of her pussy as it closed around the tip of the dildo before she pulled it back out again. She wasted no time now, no reason to tease and pretend that she was doing anything but fucking herself. She slid the toy in deep, her eyes clenching closed as she twisted it and slid it back out. Oliver's eyes were riveted on the split in her body, the toy disappearing and coming back out, wet and shiny. Faster and faster she moved, her other hand rubbing against her clit as she careened toward her second orgasm in five minutes. Her cheeks were flushed and she was biting her lip in the exact same way she usually did while she watched him work out on the salmon ladder.

Oliver was going to fucking blow and he knew it. He wanted to shove his pants down his hips and stroke his cock, jerking it hard and fast until he came, but he wasn't a pervert or a creeper. Okay, so maybe he _was _a little bit, considering he was inside her apartment, uninvited and obviously not part of Felicity's plans for the evening, but he didn't care.

At that second, Slade's sage advice came flooding back. "Two and then you." Fuck, he just wanted to be in that room. In that bed. She'd have two orgasms in before he ever joined her, but he knew, hell, he'd make it his new life's mission, to give her two more before he angled her hips up and shoved his cock inside her body.

The second time Felicity came that night, she was loud. No mewling or sobbing, just a deep, throating groan. Oliver's whole body seemed to react in response, the blood pulsing in his dick so hard that he was light-headed. He reached in and gripped the head again, trying to stave off from coming himself as he watched her lose herself. Her body rocked with pleasure, her gorgeous tits bouncing when her hips jutted upward. She pushed the fat dildo in deeply, her cunt swallowing it up until it stayed there and Oliver was unable to look away from it. He pictured his body over hers, in her so deep that his balls pressed against her ass, her lips pressed against his jaw as she clutched him, her fingers grappling for purchase against his skin while he took her over the edge. God, he was so fucking hard, throbbing as if it were his cock she was pulsating around, his cock she was milking.

_Shit_. He needed to leave. He had to get out of there before she came to her senses. She was still, unmoving except for the rise and fall of her chest. She stayed that way for a few seconds before she reached down and pulled the dildo out. She grunted as it cleared her opening, and then she dropped it into the blankets and placed a hand over her eyes.

Oliver could tell that she was exhausted. She was sated.

He should go.

He told himself to get the hell out of there and ran through all the reasons why this was one of his worst ideas ever, but his feet still refused to move back toward the window. His dick was still hard, pressing against the pants as it fought to break free. He only had a second to make a decision and, in that moment, he knew that, regardless of which choice he made, it would be the wrong one. If he went out that window, he'd never know what could have been, and if he pushed open that door, he'd never be able to make things go back the way they were before.

That thought, the very idea that giving into the thick lust choking his brain could forever upend something he valued so completely, was what finally forced him to move.

He retreated. Back to the window. His quiver went back over his shoulder. His mask slid back down over his eyes. His hood went up. Once his bow was firmly in his hand, he pushed open the window and hopped out into the storm. Regret dogged his steps as he climbed back up to the roof, but he was rappelling away from life-altering temptation before he could stop himself. The old Oliver would've pushed open Felicity's bedroom door and offered his cock to her, but the new Oliver had the weight and responsibility of his team on his shoulders.

When his feet hit concrete, he climbed onto his bike and roared down the street. The lightning flashed around him, his skin now charged from something other than the storm. Either way, things were going to be different now. He could no longer pretend what he felt for Felicity was just friendship. There was no way to pretend that he hadn't just seen this beautiful woman, who danced along the fringes of his heart, in the most unbridled way imaginable. Regardless of how he played it, one thing was very clear: _he was screwed._


End file.
